Related Experiment Video
Updated: Nov 22, 2025

Biosynthesis of a Flavonol from a Flavanone by Establishing a One-pot Bienzymatic Cascade
Published on: August 14, 2019
A comparative theoretical mechanism on simplified flavonoid derivatives and isoxazolone analogous as Michael system
Kelton L B Santos1,2, Auriekson N Queiroz3, Cleison C Lobato3,4
1Departamento de Ciências Exatas e Tecnológicas, Universidade Federal do Amapá, Macapá, AP, 68903-419, Brazil. keltonbelem@hotmail.com.
Abstract:
Flavonoids are a big class of natural product and have a wide range of biological activities. Some of these applications depend on its antioxidant capacity. Nevertheless, another mechanism can be involved by means of alkylation reaction on α,β-unsaturated carbonyl system. This study aimed to evaluate the antioxidant capacity and the chemical reactivity among simplified flavonoid derivatives and isoxazolone analogous as Michael system by using B3LYP functional and 6-311 g(d,p) basis set. Frontier molecular orbital, ionization potential (IP), spin density contributions, and Fukui index explain the antioxidant capacity and reactivity index on isoxazolone and its related derivatives. The best contribution at β-alkene moiety is related to better reactivity of α,β-unsaturated carbonyl group. A decrease in antioxidant capacity is related to an increase in the chemical reactivity index. The frontier molecular orbitals show that aurone is more reactive than isoxazolone. In accordance with Fukui index, isoxazolone can be better inhibitor as Michael system when compared to flavonoid derivatives. Graphical abstract.
More Related Videos
Related Concept Videos
Conjugate Addition of Enolates: Michael Addition
Oxidation of Phenols to Quinones
o-hydroxy phenols are oxidized to o-quinones and p-hydroxy phenols to p-quinones. Such redox reactions involve the transfer of two electrons and two protons. The reversible redox...
ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH3
Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation
Phase I Reactions: Oxidation of Aliphatic and Aromatic Carbon-Containing Systems
Oxidation reactions are fundamental in aromatic carbon-containing systems. An example is the hydroxylation of phenobarbital, a process that transforms it into...
Nonlinear Pharmacokinetics: Michaelis-Menten Equation
Vmax represents the maximum achievable process rate, while KM, known as the Michaelis constant, signifies the drug concentration at which the process rate reaches half its maximum. This relationship between Vmax, KM, and Cp gives rise to three distinct...

